Overview of He Turned One Real Estate Deal Into 13 in Just 6 Years
This BiggerPockets Real Estate Rookie episode follows Jake, a longtime listener who went from working as an indoor climbing coach to becoming a real estate agent, investor, and flipper in Bolingbrook, Illinois. He bought his first property at 23, turned it into a long-term BRRRR-style rental, then partnered with his dad on flips that eventually led to roughly a dozen completed projects and their 13th underway. The conversation focuses on how he got started, how he learned through trial and error, and what rookies should know before taking on a renovation.
Jake’s Path Into Real Estate
- Jake says he was interested in real estate from a young age and started learning through:
- Podcasts
- YouTube
- Books
- Before investing full-time, he:
- Worked in the indoor rock climbing industry
- Became a full-time real estate agent
- Opened a brokerage
- His first purchase happened just after turning 23:
- A house bought with his then-girlfriend
- Later became a rental property
- Served as his first “test” project before scaling into flips
The First Deal: A Long-Term BRRRR
What It Was
- Bought in the $130,000s in 2018
- Renovated it for about $12,000 in materials
- Did the work mostly himself with help from:
- His dad
- Family members
- A little bit of outside help when needed
- Refi’d at a 2.99% interest rate during the low-rate era
- Later moved out and rented it for $2,200, later $2,300
- Cash flow initially was about $606/month
Renovation Scope
The first renovation included:
- Opening a wall to create a more open layout
- Kitchen update:
- Cabinets
- Countertops
- Appliances
- New flooring throughout
- Bathroom updates:
- Toilets
- Vanities
What He Learned
- Cabinets were easier than expected
- Finishing details after moving in were harder than expected
- The biggest advantage was learning by doing
- He relied on:
- YouTube
- Family experience
- Trial and error
- His advice: if it’s safe, don’t be afraid to try basic DIY tasks
Partnering With His Dad
Jake’s dad brought hands-on trade experience, while Jake brought the real estate and numbers side.
Why the Partnership Worked
- His dad had spent years in a painting business and was comfortable in the trades
- Jake understood investing, pricing, and the real estate market
- Both shared the same values:
- Do quality work
- Do things the right way
- Build a good product
- They had a learning curve, but now have a strong working rhythm
- Jake says working with family can work well if the relationship is already solid and both sides communicate clearly
The First Flip: From Confidence to Reality Check
Deal Basics
- Location: Bolingbrook, Illinois
- Bought on the MLS
- Purchased in the $130,000s
- Paid about $4,000 over asking
- Used a HELOC on his dad’s primary residence to buy it
- Renovation costs were funded through savings/refi proceeds
Why It Was Different From the BRRRR
- The first flip was more stressful and time-sensitive
- They worked:
- 7 days a week
- 14–15 hours a day
- For about 5 weeks
- They hired out some licensed trades:
- Electrician
- Window/glass work
- They still did much of the work themselves
Results
- Listed around $200,000
- Had multiple buyer issues before closing:
- Financing fall-throughs
- Buyers backing out
- Ultimately sold for about $25,000 profit
The Second Flip: Bigger Problems, Bigger Lessons
What Went Wrong
- Bought in the $150,000s
- Renovation expanded quickly once walls opened up
- Found serious surprises, including:
- A shower drain improvised with a flexible garden hose
- Plumbing and electrical issues beyond DIY scope
- Realized they needed professionals for more of the work
The Permit Decision
Instead of hiding problems, Jake and his dad decided to involve the local municipality:
- Called the village out to inspect the project
- Wanted to do everything properly
- Pulled permits and worked with inspectors from the start
- This became their standard process going forward
Budget and Outcome
- Permit costs were relatively modest: roughly $500–$1,000
- Licensed trades were much more expensive than expected
- Renovation budget:
- Expected much less
- Ended up around $40,000
- Sold for about $270,000
- Profit was around $50,000–$55,000
- It became a record sale for the neighborhood
Biggest Lessons for Rookie Investors
1. Expect Problems
- Real estate projects always have surprises
- The key is not avoiding all problems, but getting better at solving them
2. Be Conservative With Numbers
- Jake says he always underwrites conservatively now
- He prefers a “happy surprise” over a bad one
- He budgets extra for unexpected issues
3. Don’t Ignore Permits and Inspectors
- Getting the village involved helped them:
- Sleep better at night
- Sell with confidence
- Improve the home toward current code
- A consult with inspectors can prevent expensive mistakes later
4. Build Contractor Relationships Carefully
Jake’s best contractor-finding methods:
- Ask neighbors who they’d hire again
- Use word of mouth
- Meet tradespeople at hardware stores
- Value reliability over online presence
His filter is simple:
- “Would you call them again?”
5. Family Partnerships Can Work
- Working with his dad strengthened their relationship
- Clear communication and shared values matter more than the “family” label itself
The Open House Water Disaster
One of the most memorable moments came during an open house:
- Jake was 45 minutes away when heavy rain caused water intrusion in a finished home
- The property had no basement, so the flooding was unexpected
- He had to:
- Shut down the open house
- Call his dad to pump water out
- Work with the village engineer to solve the drainage issue
- The village agreed to dig a swale between the houses to redirect water
- That solution helped save the sale
Main Takeaway From the Incident
- Problems will happen
- Telling people early can open the door to solutions
- Municipalities may be more helpful than investors expect if approached professionally
Current Strategy and Market Outlook
- Jake says the Chicagoland market is still relatively strong
- Days on market have risen a bit, but it’s still generally a seller’s market
- He remains conservative in his underwriting
- He continues to:
- Hire out licensed work
- Do some work himself
- Focus on good product quality
- Keep building relationships with trusted contractors
Final Takeaways
Jake’s story shows how one property can snowball into a real estate business when paired with persistence, learning, and disciplined risk-taking. His growth came from:
- Starting small
- Learning DIY skills
- Partnering with someone he trusted
- Being conservative with numbers
- Facing problems directly instead of hiding them
For rookies, the big lesson is that success in flips often comes less from perfect execution and more from adapting quickly when the deal stops following the plan.